EP ORGANIC CHEMISTRY -MOD.MASTERING 18W
9th Edition
ISBN: 9780136781776
Author: Wade
Publisher: PEARSON CO
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 9.7A, Problem 9.7P
Show how you might synthesize the following compounds, using acetylene and any suitable
- a. hex-1-yne
- b. hex-2-yne
- c. hex-3-yne
- d. 4-methylhex-2-yne
- e. 5-methylhex-2-yne
- f. cyclodecyne
Expert Solution & Answer
![Check Mark](/static/check-mark.png)
Want to see the full answer?
Check out a sample textbook solution![Blurred answer](/static/blurred-answer.jpg)
Students have asked these similar questions
1. 2-bromobutane + cyclohexanol + NaH à (major product)
c. 2-butoxycyclohexane
a.. 2-butene
reaction
b. 1-butene
d. no
e. something else!
2. t-butylbromide + sodium ethoxide in ethanol à (major product)
a. 2-methylpropene
reaction
b. t-butyl ethyl ether
c. 1-methylbutene
d. no
e. something else!
3. potassium t-butoxide + 1-bromobutane in t-butyl alcohol room
temperature à (major product)
a. 1-butene
reaction
c. 2-methylpropene d. no
b. butyl t-butyl ether
e. something else!
4. t-butyl bromide + boiling hot water à (major product)
a. 2-methylpropene
reaction
b. t-butyl ethyl ether
c. t-butanol
d. no
e. something else!
5. 2-chloropropane + acetic acid (2 eq) / KOH (1 eq) / DMF à(major
product)
c.
b.
d. no reaction
e. something
а.
HO.
else!
Br
KOH / DMSO
6.
b. 2-methyl-1-propanol
d. 1,2-
a. 2-methylpropene
propanediene
c. no reaction
e. something else!
7. cyclopentanol+ NaH + DMSO + bromopropane à(major product)
a. cyclopentene
reaction
b. propene
e. something else!!
c. propyl cyclopentyl…
For each reaction identify the reaction type.
Reaction
Туре
a. Methylbenzene and bromine in the presence of ultraviolet light forming 1-
bromo-2-methylbenzene and hydrogen bromide.
b. 2-methyldecane plus hydrogen reacts to produce heptane and butane
c. Hex-2-ene plus hydrogen chloride produces 2-chlorohexane.
d. Propane plus pentane reacts to produce 1,2-dimethylcyclohexane and
hydrogen
1. What would be the major product in the given reaction?
1) 9-BBN
2) H,О2, NaOH, Н,о
a. 2-Phenylethanal
b. 1-Phenylethanol
c. Ethylbenzene
d. Acetophenone
2. What would be the product for the following reaction?
`NH2
HO.
OH
но
а.
b.
С.
d.
Chapter 9 Solutions
EP ORGANIC CHEMISTRY -MOD.MASTERING 18W
Ch. 9.1 - a. Count the elements of unsaturation in...Ch. 9.2 - Prob. 9.2PCh. 9.4B - What reaction would acetylene likely undergo if it...Ch. 9.6 - Prob. 9.4PCh. 9.6 - Predict the products of the following acid-base...Ch. 9.7A - Solved Problem9-1 showed the synthesis of...Ch. 9.7A - Show how you might synthesize the following...Ch. 9.7B - Prob. 9.8PCh. 9.7B - Show how you would synthesize...Ch. 9.8 - When 2,2-dibromo-1-phenylpropane is heated...
Ch. 9.8 - When 2,2-dibromo-1-phenylpropane is heated...Ch. 9.9C - Show how you would convert a. oct-3-yne to...Ch. 9.9C - The fragrance of (Z)-1-phenylhex-2-en-1-ol...Ch. 9.9D - In the addition of just 1 mole of bromine to 1...Ch. 9.9E - Propose a mechanism for the entire reaction of...Ch. 9.9E - Predict the major product(s) of the following...Ch. 9.9E - Propose a mechanism for the reaction of pent-1-yne...Ch. 9.9E - Show how hex-1-yne might be converted to a....Ch. 9.9F - When pent-2-yne reacts with mercuric sulfate in...Ch. 9.9F - Prob. 9.20PCh. 9.9F - Prob. 9.21PCh. 9.9F - Prob. 9.22PCh. 9.10A - Predict the product(s) you would expect from...Ch. 9.10B - Prob. 9.24PCh. 9.10B - Prob. 9.25PCh. 9 - Prob. 9.26SPCh. 9 - Give common names for the following compounds. a....Ch. 9 - Prob. 9.28SPCh. 9 - Prob. 9.29SPCh. 9 - Using cyclooctyne as your starting material, show...Ch. 9 - Prob. 9.31SPCh. 9 - Prob. 9.32SPCh. 9 - Predict the products of reaction of pent-1-yne...Ch. 9 - Show how you would accomplish the following...Ch. 9 - Show how you would synthesize the following...Ch. 9 - Predict the products formed when CH3CH2C C : Na+...Ch. 9 - Prob. 9.37SPCh. 9 - Prob. 9.38SPCh. 9 - When compound Z is treated with ozone, followed by...Ch. 9 - Show how you would convert the following starting...Ch. 9 - The following functional-group interchange is a...Ch. 9 - Using any necessary inorganic reagents, show how...Ch. 9 - Prob. 9.43SP
Additional Science Textbook Solutions
Find more solutions based on key concepts
Calculate the lattice energy of CaCl2 using a Born-Haber cycle and data from Appendices F and L and Table 7.5. ...
Chemistry & Chemical Reactivity
Calculate the lattice energy of CaCl2 using a Born-Haber cycle and data from Appendices F and L and Table 7.5. ...
Chemistry & Chemical Reactivity
Practice Problem ATTEMPT
Write the rate expressions for each of the following reactions:
(a)
(b)
(c)
Chemistry
Determine the number of protons, neutrons, and electrons in the following atoms: a. a hydrogen atom that has a ...
General, Organic, and Biological Chemistry (3rd Edition)
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- 2. Which of the following alkynes will form only 1 product in acid-catalyzed hydration? a. 2-pentyne b. 3-hexyne c. 3-pentyne d. 1-hexyne 3. Which of the following statements best describes the general reactivity of alkynes? a. An alkyne reacts as an electrophile and is, therefore, electron poor. b. Alkynes undergo electrophilic addition reactions just like alkenes. c. An alkyne reacts as an electrophile and is therefore electron-rich. d. An alkyne reacts as a nucleophile and is therefore electron-poor.arrow_forwardThe major product of the reaction below is OH H* heat A. 3-methyl-1-butene B. 2-methyl-3-butene C. 3-methyl-2-butene D. 2-methyl-2-butenearrow_forward2. Name each alkyne. a. CH3CH₂CH₂C=CH b. CH3CH₂CH₂C=CCH3 3. Predict the product of the following reactions. a. CH = CCH3 + HCI b. CH CCH₂CH3 + O2arrow_forward
- Choose the two alkyl bromides and the hydrogenation method that must be used to synthesize these alkenes from acetylene. Enter your answer as two letters in alphabetical order, followed by a number; i.e. ac2, not ca2. Do not use punctuation. Alkyl Halides a. CH3CH2B b. CH3(CH2)4Br c. CH3(CH2)5Br d. CH3(CH2);Br e. CH3(CH2);Br f. CH3(CH2);Br g. CH3(CH2)12Br Hydrogenation Method 1. H2, Lindlar's catalyst 2. Na, NH3 (1) Alkene #1: CH3 H3C Alkene #2: CH3 H3Carrow_forwardChoose the two alkyl bromides and the hydrogenation method that must be used to synthesize these alkenes from acetylene. Enter your answer as two letters in alphabetical order, followed by a number; i.e. ac2, not ca2. Do not use punctuation. Alkyl Halides a. CH3CH₂Br b. CH3(CH₂)4Br c. CH3(CH2)sBr d. CH3(CH₂) Br e. CH3(CH₂)7Br f. CH₂(CH₂) Br g. CH3(CH₂)12Br Hydrogenation Method 1. H₂, Lindlar's catalyst 2. Na, NH3 (1) CH3 Alkene #1: H₂C Alkene #2: H₂C CH3arrow_forward1. Which reaction conditions would be best for turning ethene into ethanol? a.H2O, HBr b. CH3OH, H2SO4 c.CH3OH, HBR d. H2O, H2SO4 2. Which alkene would be non-regioselective in a reaction with HBr? a. 2-ehyl-2-methyl-2-butene b.2-ethyl-3-methyl-2-butene c. 2,3-dimethyl-2-butene d.1,2-dimethyl-2-butenearrow_forward
- 10. What is the product of the following reaction? H₂NNH₂, KOH heat A.3-methylpentane B.3-methyl-2-pentanol C.3-methyl-2-pentene D. 3-methyl-1-pentynearrow_forwardIdentify the role/function of the indicated molecule in the reaction? 1. LIAIH, ether 2. Но NaN3 Br -NH2 a. Nucleophile b. Electrophile c. Base O d. Acidarrow_forwardBr KOH / DMSO 6. b. 2-methyl-1-propanol d. 1,2- a. 2-methylpropene propanediene c. no reaction e. something else! 7. cyclopentanol + NaH + DMSO+ bromopropane à(major product) a. cyclopentene reaction b. propene c. propyl cyclopentyl ether d. no e. something else!! 8. 2-bromo-3-methylbutane + KOH / DMSO à(major product) a. 2-methyl-1-butene d. no reaction b. 2-methyl-2-butene c. 3-methyl-2-butanol e. something else!! 9. 2-chloro-3-methylbutane + KI / DMSO à(major product) a. 2-methyl-1-butene b. 2-methyl-2-butene c. 3-methyl-2-iodobutane d. no rxn e. something else!! 10. (S)-2-iodobutane + NaN; / DMF à (major product) N3 c. f. something else!! а. b. с. d. е. no rxn 11. cyclohexene + NBS/ CCl, / light followed by K* t-butoxide / t-butanol with heating à a. cyclohexene b. 1,3-cyclohexadiene cyclohexane e. something else! c. 1,2-cyclohexadiene d.arrow_forward
- 43. Identify the reagent that will produce the following brominated product in greatest amount. Br A. Br2/uv B. Br2/FeBr3 C. NBS D. B12/CC14 44. Under acidic condition, which of the following compounds can not be oxidized by KMnO4. A. toluene B. 2-butene C. methylcyclohexane D. 2-butyne 45. What alkene product can be produced from the reaction of 2-hexyne with Lindlar's catalyst? A. cis-2-Hexene B. trans-2-Hexene C. Hexane D. A and Barrow_forward8. Write an equation representing each of the following reactions: a. 1-Heptene+H2O (H+) b. 3-Heptene+H2 c. 2-Methyl-2-hexene+HCI d. 3-Methyl-1,4-cyclohexadiene+C12 e. 2,4-Heptadiene+Br2 f. 3-Methylcyclopentene+H2O (H+)arrow_forwardAlkyl halide can be prepared from the addition of H-X to alkenes. Identify the product in the reaction. H-Br Select one: a. 1,2-dibromo-2-methylpropane b. 1-bromo-2-methylpropane c. t-butyl bromide (or 2-bromo-2-methylpropane) d. 2-methylpropanearrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage LearningChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill EducationPrinciples of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
- Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill EducationChemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage LearningElementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY
![Text book image](https://www.bartleby.com/isbn_cover_images/9781305957404/9781305957404_smallCoverImage.gif)
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
![Text book image](https://www.bartleby.com/isbn_cover_images/9781259911156/9781259911156_smallCoverImage.gif)
Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education
![Text book image](https://www.bartleby.com/isbn_cover_images/9781305577213/9781305577213_smallCoverImage.gif)
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
![Text book image](https://www.bartleby.com/isbn_cover_images/9780078021558/9780078021558_smallCoverImage.gif)
Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education
![Text book image](https://www.bartleby.com/isbn_cover_images/9781305079373/9781305079373_smallCoverImage.gif)
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
![Text book image](https://www.bartleby.com/isbn_cover_images/9781118431221/9781118431221_smallCoverImage.gif)
Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY
IR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=_TmevMf-Zgs;License: Standard YouTube License, CC-BY